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Synthesis and evaluation as biodegradable herbicides of halogenated analogs of L-meta-tyrosine

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Abstract

l-meta-tyrosine is an herbicidal nonprotein amino acid isolated some years ago from fine fescue grasses and characterized by its almost immediate microbial degradation in soil (half-life <24 h). Nine monohalogenated or dihalogenated analogs of this allelochemical have been obtained through a seven-step stereoselective synthesis from commercial halogenated phenols. Bioassays showed a large range of biological responses, from a growth root inhibition of lettuce seedling similar to that noted with m-tyrosine [2-amino-3-(2-chloro-5-hydroxyphenyl)propanoic acid or compound 8b] to an increase of the primary root growth concomitant with a delay of secondary root initiation [2-amino-3-[2-fluoro-5-hydroxy-3-(trifluoromethyl)phenyl]propanoic acid or compound 8h]. Compound 8b was slightly less degraded than m-tyrosine in the nonsterilized nutritive solution used for lettuce development, while the concentration of compound 8h remained unchanged for at least 2 weeks. These data indicate that it is possible to manipulate both biological properties and degradation of m-tyrosine by halogen addition.

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Acknowledgments

The authors would like to thank Emilie Dugaro for his kind collaboration in organic synthesis.

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Authors and Affiliations

  1. Institut de Chimie des Milieux et des Matériaux de Poitiers, Unité Mixte de Recherche CNRS 7285, Université de Poitiers, 40 Avenue du Recteur Pineau, 86022, Poitiers Cedex, France

    Julie Movellan, Françoise Rocher, Zohra Chikh, Cécile Marivingt-Mounir & Jean-François Chollet

  2. Laboratoire Écologie et Biologie des Interactions, Unité Mixte de Recherche CNRS 7267, Université de Poitiers, 40 Avenue du Recteur Pineau, 86022, Poitiers Cedex, France

    Jean-Louis Bonnemain

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  1. Julie Movellan
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  2. Françoise Rocher
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  3. Zohra Chikh
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  4. Cécile Marivingt-Mounir
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  5. Jean-Louis Bonnemain
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  6. Jean-François Chollet
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Correspondence to Jean-François Chollet.

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Responsible editor: Philippe Garrigues

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Movellan, J., Rocher, F., Chikh, Z. et al. Synthesis and evaluation as biodegradable herbicides of halogenated analogs of L-meta-tyrosine. Environ Sci Pollut Res 21, 4861–4870 (2014). https://doi.org/10.1007/s11356-012-1302-5

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